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Lewis Acid Catalyzed Intermolecular Olefin Hydroamination: Scope, Limitation, and Mechanism
Author(s) -
Cheng Xiaojuan,
Xia Yuanzhi,
Wei Hua,
Xu Bin,
Zhang Chongguang,
Li Yahong,
Qian Guimin,
Zhang Xiaohua,
Li Kai,
Li Wu
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200701080
Subject(s) - hydroamination , chemistry , carbocation , lewis acids and bases , catalysis , olefin fiber , norbornene , intermolecular force , cationic polymerization , organic chemistry , lewis acid catalysis , allylamine , copolymer , molecule , polyelectrolyte , polymer
Intermolecular olefin hydroamination was studied by various Lewis acids. The results of ZrCl 4 , FeCl 3 , BiCl 3 , and AlCl 3 catalyzed reactions of norbornene with aromatic amines were compared, and BiCl 3 was found to be the most effective catalyst to give high yields for various amines, whereas ZrCl 4 could promote the reactions at relatively low temperatures. The FeCl 3 catalyzed reactions were the most chemoselective and excellent yields could be achieved for certain amines by using AlCl 3 . A carbocation mechanism was proposed, and the controllable syntheses of allylamine and tetrahydroquinoline from isoprene and 2,5‐dichloroaniline were achieved by application of this mechanism. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)